Programming an Arduino Duemilanove (2009)

Assume it has no bootloader, and install the Uno bootloader that is included in IDE 1.0.5.
You have a 2nd Arduino? Use Nick Gammon's sketch to bootload the Duemilanove.

Type of USB/Serial interface is not material to the bootloader. I bootload all my 328P DIPs as Uno, no matter the actual board I build up around them.